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Sulfonyl chloride synthesis by oxidation - Organic chemistry

Reaction of 2-acetamidonaphthalene with sulfur monochloride gives the corresponding naphthothiazathiolium chloride, which on sequential hydrolyses with sodium bicarbonate and sodium hydroxide affords 2-aminonaphthalene-1-thiol.

AB - The synthesis and characterization of long-chain alkyltrichlorosilanes of alkyl halides, benzyl halides, and α-haloacetyls designed to form silozane-anchored self-assembled monolayers (SAMs) for the selective attachment of peptides (via cysteine thiols) is described. Thin film formation by the trichlorosilanes was demonstrated by spectroscopic means and by surface wetting properties. Halide exchange could be utilized to produce the more reactive (iodide) surfaces in situ, following their deposition in a more stable (chloride or bromide) form. In solution, these functional groups were found to have a range of reactivity with model thiols which extended from half-lives of minutes to days (essentially no reactivity). The order of reactivity is I > Br > Cl within each class of compounds, and α-haloacetyl > benzyl ≫ alkyl. The reactivity of the SAMs with thiols showed the same order of reactivity. The very reactive α-iodoacetyl was also reactive with amines, but competition experiments demonstrated preference for the thiol under our reaction conditions. SAM reactivity with cysteine-containing peptides was demonstrated with a tripeptide (glutathione) and a nonapeptide (laminin fragment). Both peptides show maximum attachment after 2-3 h of exposure to millimolar concentrations. The attachment was completely blocked by prior treatment of these peptides with dinitrophenylmaleimide or by air oxidation of the thiol. Given that these peptides contain all the nucleophilic side chains found in proteins (thiol, alcohol, phenol, carboxyl, and amine), the selective blocking experiments indicate that these SAMs will be useful for the directed attachment through cysteine side chains in proteins and peptides.

13.03.2014 · Structural Biochemistry/Proteins/Synthesis

Sulfide synthesis by S-alkylation or 1,4-addition

Synthesis of Non-linear Protein Dimers through a Genetically Encoded ..

Protocols for postsynthetic modification of 2‐amino‐containing oligoribonucleotides with either an alkyl‐phenyl disulfide or an alkyl thiol group are described. These groups react under mild conditions to form disulfide cross‐links by thiol‐disulfide interchange. These reactants do not form a disulfide bond when incorporated on opposite faces of a short continuous RNA helix, but do form disulfide bonds rapidly when they are placed in proximity. In addition, by incorporating these groups at various positions on large RNAs by semisynthesis, the dynamics of thermal motions can be detected. Such motions are believed to be linked to biological function, and the protocols presented in this unit are among the few simple ways to assess such dynamics.

Protocols for postsynthetic modification of 2‐amino‐containing oligoribonucleotides with either an alkyl‐phenyl disulfide or an alkyl thiol group are described. These groups react under mild conditions to form disulfide cross‐links by thiol‐disulfide interchange. These reactants do not form a disulfide bond when incorporated on opposite faces of a short continuous RNA helix, but do form disulfide bonds rapidly when they are placed in proximity. In addition, by incorporating these groups at various positions on large RNAs by semisynthesis, the dynamics of thermal motions can be detected. Such motions are believed to be linked to biological function, and the protocols presented in this unit are among the few simple ways to assess such dynamics.

SDS Search - EH&S - WKU - Western Kentucky University

The synthesis and characterization of long-chain alkyltrichlorosilanes of alkyl halides, benzyl halides, and α-haloacetyls designed to form silozane-anchored self-assembled monolayers (SAMs) for the selective attachment of peptides (via cysteine thiols) is described. Thin film formation by the trichlorosilanes was demonstrated by spectroscopic means and by surface wetting properties. Halide exchange could be utilized to produce the more reactive (iodide) surfaces in situ, following their deposition in a more stable (chloride or bromide) form. In solution, these functional groups were found to have a range of reactivity with model thiols which extended from half-lives of minutes to days (essentially no reactivity). The order of reactivity is I > Br > Cl within each class of compounds, and α-haloacetyl > benzyl ≫ alkyl. The reactivity of the SAMs with thiols showed the same order of reactivity. The very reactive α-iodoacetyl was also reactive with amines, but competition experiments demonstrated preference for the thiol under our reaction conditions. SAM reactivity with cysteine-containing peptides was demonstrated with a tripeptide (glutathione) and a nonapeptide (laminin fragment). Both peptides show maximum attachment after 2-3 h of exposure to millimolar concentrations. The attachment was completely blocked by prior treatment of these peptides with dinitrophenylmaleimide or by air oxidation of the thiol. Given that these peptides contain all the nucleophilic side chains found in proteins (thiol, alcohol, phenol, carboxyl, and amine), the selective blocking experiments indicate that these SAMs will be useful for the directed attachment through cysteine side chains in proteins and peptides.

Protocols for postsynthetic modification of 2‐amino‐containing oligoribonucleotides with either an alkyl‐phenyl disulfide or an alkyl thiol group are described

2 The thiol group of cysteine also plays an important role in protein folding when an oxidation reaction of two thiol groups of close cysteine residues generates a cystine unit with a disulfide bond (R–S–S–R).

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Sulfonyl chloride synthesis by oxidation - Organic …


Zinc Oxide—From Synthesis to Application: A Review - MDPI

N2 - The synthesis and characterization of long-chain alkyltrichlorosilanes of alkyl halides, benzyl halides, and α-haloacetyls designed to form silozane-anchored self-assembled monolayers (SAMs) for the selective attachment of peptides (via cysteine thiols) is described. Thin film formation by the trichlorosilanes was demonstrated by spectroscopic means and by surface wetting properties. Halide exchange could be utilized to produce the more reactive (iodide) surfaces in situ, following their deposition in a more stable (chloride or bromide) form. In solution, these functional groups were found to have a range of reactivity with model thiols which extended from half-lives of minutes to days (essentially no reactivity). The order of reactivity is I > Br > Cl within each class of compounds, and α-haloacetyl > benzyl ≫ alkyl. The reactivity of the SAMs with thiols showed the same order of reactivity. The very reactive α-iodoacetyl was also reactive with amines, but competition experiments demonstrated preference for the thiol under our reaction conditions. SAM reactivity with cysteine-containing peptides was demonstrated with a tripeptide (glutathione) and a nonapeptide (laminin fragment). Both peptides show maximum attachment after 2-3 h of exposure to millimolar concentrations. The attachment was completely blocked by prior treatment of these peptides with dinitrophenylmaleimide or by air oxidation of the thiol. Given that these peptides contain all the nucleophilic side chains found in proteins (thiol, alcohol, phenol, carboxyl, and amine), the selective blocking experiments indicate that these SAMs will be useful for the directed attachment through cysteine side chains in proteins and peptides.

Bioorganic & Medicinal Chemistry Letters | Vol 20, Iss …

One mechanism that may be involved in acute damage is nicotinamide adenine dinucleotide (NAD) depletion. The nuclear enzyme poly-(adenosine diphosphoribose) polymerase is activated by DNA strand breaks, such as those produced by sulfur and nitrogen mustards. The enzyme cleaves NAD between nicotinamide and adenine diphosphoribose (ADP) and joins the ADP molecules into polymers of ADP-ribose, which are then linked to nuclear proteins, including the enzyme itself. This process can rapidly deplete cellular pools of NAD, which is required for ATP synthesis. The subsequent depletion of ATP rapidly produces loss of energy-dependent functions in the cell and results in cell death.

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